CA2703560C - Methode de production de 2-desoxy-5-azacytidine (decitabine) - Google Patents

Methode de production de 2-desoxy-5-azacytidine (decitabine) Download PDF

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Publication number
CA2703560C
CA2703560C CA2703560A CA2703560A CA2703560C CA 2703560 C CA2703560 C CA 2703560C CA 2703560 A CA2703560 A CA 2703560A CA 2703560 A CA2703560 A CA 2703560A CA 2703560 C CA2703560 C CA 2703560C
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Canada
Prior art keywords
formula
beta
deoxy
compound
azacytidine
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CA2703560A
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CA2703560A1 (fr
Inventor
Oliver Jungmann
Norbert Kraut
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Cilag AG
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Cilag AG
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Application filed by Cilag AG filed Critical Cilag AG
Publication of CA2703560A1 publication Critical patent/CA2703560A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/12—Triazine radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Molecular Biology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Saccharide Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé permettant d'obtenir de la 2'-désoxy-5-azacytidine (décitabine) en produisant un composé répondant à la formule (I) : R étant un substituant amovible, connu en soi ; et R1 étant un substituant amovible ; puis en produisant une base silylée représentée par la formule (II) : R2 étant un groupe de protection, de préférence un résidu de triméthylsilyle (TMS) ; en faisant réagir le composé répondant à la formule (I) avec le composé répondant à la formule (II) dans un solvant anhydre approprié et en présence d'un catalyseur approprié ; et en éliminant les substituants R du composé obtenu en vue d'obtenir le composé 2' -désoxy-5-azacytidine (décitabine), le procédé étant caractérisé en ce que ledit catalyseur est sélectionné parmi le groupe comprenant un sel d'un acide sulfonique aliphatique ou un sel d'un acide fort inorganique.
CA2703560A 2007-10-10 2008-10-10 Methode de production de 2-desoxy-5-azacytidine (decitabine) Active CA2703560C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP07019826.2 2007-10-10
EP07019826A EP2050757A1 (fr) 2007-10-10 2007-10-10 Procédé de fabrication de 2' -désoxy-5-azacytidine (Décitabine)
PCT/EP2008/063581 WO2009047313A2 (fr) 2007-10-10 2008-10-10 Procédé de production de 2' -désoxy-5-azacytidine (décitabine)

Publications (2)

Publication Number Publication Date
CA2703560A1 CA2703560A1 (fr) 2009-04-16
CA2703560C true CA2703560C (fr) 2016-09-13

Family

ID=39496166

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2703560A Active CA2703560C (fr) 2007-10-10 2008-10-10 Methode de production de 2-desoxy-5-azacytidine (decitabine)

Country Status (31)

Country Link
US (1) US20100222565A1 (fr)
EP (2) EP2050757A1 (fr)
JP (1) JP5453279B2 (fr)
KR (1) KR101551779B1 (fr)
CN (1) CN102037003B (fr)
AP (1) AP2719A (fr)
AU (1) AU2008309552B2 (fr)
BR (1) BRPI0818595B1 (fr)
CA (1) CA2703560C (fr)
CO (1) CO6270260A2 (fr)
CY (1) CY1116540T1 (fr)
DK (1) DK2201020T3 (fr)
EA (1) EA018924B1 (fr)
EC (1) ECSP10010091A (fr)
ES (1) ES2512591T3 (fr)
GT (1) GT201000076A (fr)
HN (1) HN2010000654A (fr)
HR (1) HRP20140856T1 (fr)
IL (1) IL204918A0 (fr)
MX (1) MX2010003887A (fr)
MY (1) MY150047A (fr)
NI (1) NI201000049A (fr)
NZ (1) NZ584373A (fr)
PL (1) PL2201020T3 (fr)
PT (1) PT2201020E (fr)
SI (1) SI2201020T1 (fr)
SV (1) SV2010003523A (fr)
UA (1) UA101482C2 (fr)
UY (1) UY31388A1 (fr)
WO (1) WO2009047313A2 (fr)
ZA (1) ZA201002517B (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2048151A1 (fr) * 2007-10-10 2009-04-15 Cilag AG Procédé pour la production de nucléosides par glycosylation directe de la base nucléosidique
US8586729B2 (en) * 2008-10-03 2013-11-19 Scinopharm Taiwan Ltd. Synthesis of decitabine
EP2424845A4 (fr) * 2009-04-27 2014-03-05 Reddys Lab Ltd Dr Préparation de décitabine
IT1399195B1 (it) * 2010-03-30 2013-04-11 Chemi Spa Processo per la sintesi di azacitidina e decitabina
CN101948493A (zh) * 2010-06-28 2011-01-19 江苏奥赛康药业有限公司 一种高纯度地西他滨的工业化生产方法
KR101241321B1 (ko) * 2010-08-05 2013-03-11 케이피엑스 라이프사이언스 주식회사 수율 및 순도가 개선된 데시타빈의 제조방법
CN102391338A (zh) * 2011-09-30 2012-03-28 重庆泰濠制药有限公司 一种地西他滨中间体粗品的纯化方法
CN104211743A (zh) * 2013-05-29 2014-12-17 南京工业大学 一种地西他宾的合成
CN103601768B (zh) * 2013-11-13 2015-09-30 齐鲁天和惠世制药有限公司 一种阿米卡星的制备方法
WO2017096357A1 (fr) 2015-12-03 2017-06-08 Epidestiny, Inc. Compositions contenant de la décitabine, de la 5-azacytidine et de la tétrahydrouridine
CN109912672B (zh) * 2019-04-02 2021-07-27 江西师范大学 一种以邻炔基苯酚醚作为离去基的碱基糖苷化的方法
CN112209976B (zh) * 2019-07-10 2023-05-26 鲁南制药集团股份有限公司 一种地西他滨中间体化合物ⅴ
CN112209977B (zh) * 2019-07-10 2023-05-26 鲁南制药集团股份有限公司 一种地西他滨中间体化合物ⅵ

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2012888C3 (de) * 1970-03-14 1981-04-02 Schering Ag, 1000 Berlin Und 4619 Bergkamen Verfahren zur Herstellung von 5-Azapyrimidinnucleosiden
DE2508312A1 (de) * 1975-02-24 1976-09-02 Schering Ag Neues verfahren zur herstellung von nucleosiden
DE2757365A1 (de) * 1977-12-20 1979-06-21 Schering Ag Neues verfahren zur herstellung von nucleosiden
UA41261C2 (uk) * 1992-06-22 2001-09-17 Елі Ліллі Енд Компані Спосіб одержання збагачених бета-аномером нуклеозидів
US5426183A (en) * 1992-06-22 1995-06-20 Eli Lilly And Company Catalytic stereoselective glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides
US5606048A (en) 1992-06-22 1997-02-25 Eli Lilly And Company Stereoselective glycosylation process for preparing 2'-Deoxy-2', 2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides
JP2666160B2 (ja) * 1993-11-05 1997-10-22 財団法人野口研究所 ５−ｏ−ピリミジル−２，３−ジデオキシ−１−チオフラノシド誘導体，その製造方法及び用途
JPH11514642A (ja) * 1995-11-02 1999-12-14 チョング クン ダング シーオーアールピー． 新規なヌクレオシド誘導体及びその製造方法
ATE292631T1 (de) * 1998-08-12 2005-04-15 Gilead Sciences Inc Verfahren zu herstellung von 1,3-oxathiolane nukleosiden

Also Published As

Publication number Publication date
ZA201002517B (en) 2012-07-25
JP5453279B2 (ja) 2014-03-26
DK2201020T3 (da) 2014-10-13
HK1152312A1 (en) 2012-02-24
AP2010005226A0 (en) 2010-04-30
AP2719A (en) 2013-07-31
ES2512591T3 (es) 2014-10-24
CN102037003A (zh) 2011-04-27
AU2008309552A1 (en) 2009-04-16
WO2009047313A3 (fr) 2012-03-01
EP2050757A1 (fr) 2009-04-22
BRPI0818595B1 (pt) 2022-02-15
CA2703560A1 (fr) 2009-04-16
NZ584373A (en) 2011-08-26
UA101482C2 (ru) 2013-04-10
HRP20140856T1 (hr) 2014-10-24
HN2010000654A (es) 2012-12-03
KR101551779B1 (ko) 2015-09-09
EP2201020A2 (fr) 2010-06-30
BRPI0818595A2 (pt) 2015-04-22
EA018924B1 (ru) 2013-11-29
EA201070437A3 (ru) 2011-02-28
KR20100064387A (ko) 2010-06-14
PL2201020T3 (pl) 2014-12-31
EP2201020B1 (fr) 2014-07-16
CO6270260A2 (es) 2011-04-20
WO2009047313A2 (fr) 2009-04-16
US20100222565A1 (en) 2010-09-02
CN102037003B (zh) 2014-05-07
SV2010003523A (es) 2011-01-25
PT2201020E (pt) 2014-09-23
CY1116540T1 (el) 2017-03-15
AU2008309552B2 (en) 2013-01-17
MY150047A (en) 2013-11-29
JP2011518759A (ja) 2011-06-30
EA201070437A2 (ru) 2010-08-30
UY31388A1 (es) 2009-04-30
MX2010003887A (es) 2010-04-30
NI201000049A (es) 2010-11-10
SI2201020T1 (sl) 2014-11-28
GT201000076A (es) 2012-03-12
ECSP10010091A (es) 2010-06-29
IL204918A0 (en) 2010-11-30

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